Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011 Dec 21;52(51):6923-6926.
doi: 10.1016/j.tetlet.2011.10.065.

Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E

Affiliations

Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide E and 6-hydroxydeoxybrevianamide E

Hikaru Kato et al. Tetrahedron Lett. .

Abstract

Two reverse-prenylated indole alkaloids, deoxybrevianamide E and 6-hydroxydeoxybrevianamide E, are proposed as biosynthetic precursors for advanced metabolites isolated from the marine-derived Aspergillus sp. In order to uncover the role of the alkaloids in the biosynthetic pathway, the feeding experiments of the [(13)C](2)-[(15)N]-labeled deoxybrevianamide E and 6-hydroxydeoxybrevianamide E were performed to afford the metabolites, which were produced by oxidation and successive pinacol-type rearrangement of the isoprenyl units.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Result of the feeding experiment of doubly 13C-labeled 8 with the marine-derived fungus Aspergillus sp.
Figure 2
Figure 2
Possible biogenesis of the bicyclo[2.2.2]diazaoctane-containing alkaloid 2 from 7.
Figure 3
Figure 3
Result of the feeding experiment of [13C]2-[15N]-7, 10, 16, and 15.
Figure 4
Figure 4
Structures of three pairs of antipodal alkaloids isolated from the marine-derived Aspergillus sp. and the terrestrial-derived Aspergillus versicolor.

Similar articles

Cited by

References

    1. Birch AJ, Wright JJ. Tetrahedron. 1970;26:2329. - PubMed
    2. Birch AJ, Wright JJS. J Chem Soc, Chem Commun. 1969:644–645.
    3. Birch AJ, Russell RA. Tetrahedron. 1972;28:2999.
    1. Yamazaki M, Okuyama E, Kobayashi M, Inoue H. Tetrahedron Lett. 1981;22:135–136.
    2. Ondeyka JG, Goegelman RT, Schaeffer JM, Kelemen L, Zitano L. J Antibiot. 1990;43:1375–1379. - PubMed
    3. Liesch JM, Wichmann CF. J Antibiot. 1990;43:1380–1386. - PubMed
    4. Banks RM, Blanchflower SE, Everett JR, Manger BR, Reading C. J Antibiot. 1997;50:840–846. - PubMed
    1. Qian-Cutrong J, Huang S, Shu Y-Z, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q. J Am Chem Soc. 2002;124:14556–14557. - PubMed
    1. Martinez-Luis S, Rodriguez R, Acevedo L, Gonzalez MC, Lira-Rocha A, Mata R. Tetrahedron. 2006;62:1817–1822.
    2. Figueroa M, Del Carmen González M, Mata R. Nat Prod Res. 2008;22:709–714. - PubMed
    1. Polonsky J, Merrien MA, Prange T, Pascard C. J Chem Soc, Chem Commun. 1980:601–602.
    2. Prange T, Billion M-A, Vuilhorgne M, Pascard C, Polonsky J. Tetrahedron Lett. 1981;22:1977–1980.

LinkOut - more resources